You Can Be Very Abrasive!

That’s what she said to me. It was around 2004 and she was a mentor to me. I held her in such high regard, I admired her and when she spoke I listened. We were having lunch on a beautiful spring day in Harvard Square, dining on a restaurant patio. She was cultured, she had the pedigrees, she’d been around the world and back, and she’d totally kicked ass over her highly entrepreneurial career. Now, in her early 60s, she was as wise as she was inspiring. And she said, “you know, you can be very abrasive sometimes.” My fork stayed steady in my hand while I paused and humbly and sheepishly responded, “I know.” I sat back to hear her out.

A few years later I find myself far from the guy I was then, yet very much still that guy. I feel like I’ve come full circle in many ways. And only when you go on that journey do you really learn. A pattern has been revealed.

Today I start a new stage of my career. After two and a half years at Litle & Co., as their Vice President of Marketing, and through their late 2012 acquisition by publicly traded Vantiv, I’m getting back to what I do best – startups and entrepreneurship. My experience at Litle & Co. was nothing short of educational and enjoyable. I learned so much. Most of all, I proved something to myself, and that was the biggest gain.

For the most part I’m taking time off, to enjoy spring and summer, to see friends and family, to enjoy life, but also to make my next move a smart one. The next stage of my career is an important one. At 37 it has to be wise. Not conservative, mind you, but wise. I often fantasize about a totally different career path, one of journalism, or of science, always something that might make real change in the world. As one of my best friends often says, “the last thing we need is another app to help me find the pizza, review the pizza, get a deal on the pizza, take a picture of the pizza, and clip recipes of the pizza.” I’m often frustrated by the lack of real innovation out there, truly transformative stuff, specifically in the digital space. Stuff that really makes a difference. But it’s not enough to be frustrated, that breeds apathy. Instead I’m embarking on something new here. I’m also often frustrated by what I’ll call the cult of personality that’s come out of and surrounds the Internet’s entrepreneurial scene, here in Boston, in NY, in Silicon Valley. Scenesters, hipsters, hangers-on. Me toos. That stuff is just such a turn off. And none of it even really matters. But again, it’s not enough to be frustrated and annoyed by it.

So with that I’m launching an experiment, if you will. I call it Sure Shot Labs. Sure Shot Labs will be the vehicle that helps me navigate this transition, these bumpy roads. Through Sure Shot myself and a few trusted and passionate colleagues will try something new for all of us. We’ll build products and invest in ideas we have, on our terms. The traditional start-up model is gone. The lean startup is here. We will consult, yes, we will make our clients happy indeed, and we will take the proceeds from those engagements and invest them in the lab, in our experiments, in innovation and in products. This will be fun.

When I think about that conversation with my mentor nearly 10 years ago, I think about the young man I was. I think about how “abrasive” I was. It was unearned confidence and it was fear. Back then I had to compete with others who were smarter, bigger, stronger, more experienced, more wealthy, more well connected, and more educated. Today I still have to compete with those people. And they still might be bigger than me, stronger than me, smarter than me, wealthier than me, more well connected and more educated. But what they lack, and have never been able to compete with, is my endless tenacity, my ability to wear them out, like a wolf and its prey. And the street smarts, the innate will to work smarter, to work harder, to out-think and out-smart, to out-play, to outwit and out-will. I’ve always been out of my league. I’ve always been in over my head. I’ve rarely done things their way. I don’t plan on starting today.


Startups are Families

CitySquares isn’t the first startup company I’ve been a part of, but it’s certainly the most special, because it’s my creation. This company has taken on a life of its own. It took some time for it to develop this heartbeat and to get this personality. No doubt it’s is an entity all to itself, more so than just a tax ID with the government. From the very beginning in August 2005, a culture was starting to take shape. We’d sit at my kitchen table in Davis Square and talk about what this could be, how it would work, what kind of future should we plan for, what kind of company do we want this to be. Even when it was just three of us, and even when we had sales people making minimum wage out on the streets all day, every day, it was forming a personality. It was largely out of my control too. I could influence the culture a bit, just by being a part of the business, and setting the vision. But the personality, the culture that the company takes on is essentially a manifestation of the personalities and cultures brought into it by its staff, even those that come and go. Continue reading Startups are Families

Events and Networking for Boston Startups

It’s been over two years since we discovered WebInno and were subsequently invited by David Beisel to be a sidedish. Among other notable Boston area events, WebInno was probably the most exciting for us, and it really gave us the shot in the arm that we needed. We also met some fantastic people that evening, many of whom we stay in close contact with. In fact, we met one of our advisory board members at that first WebInno. Each time I attend a WebInno, I’m not only shocked by the spike in attendees each event seems to have but also by the genuinely good vibe in the room that lasts for hours.

My point here is that as a startup company, and as an untested business seeking an identity and a place in the Boston entrepreneurial and startup scene, WebInno was really just one of many pivotal networking events for us. As this blog continues to be about entrepreneurship, and my perspective from the trenches, I don’t want to forget about these events and opportunities. Furthermore, I really encourage other entrepreneurs to be sure they get out there – hit the streets, attend events, network, don’t be shy. It’s like anything, once you get some momentum and get into a rhythm it just gets easier.

Here are some events that I’ve either attended or would like to attend in the Boston area:

  • WebInno – Cambridge, MA, about once every 3 months or so. Well worth it! And if you’re in the Internet space, check with David to see if you can a shot at a side dish or main dish. David’s very accommodating and open minded.
  • MIT Enterprise Forum – Cambridge, MA. Hey, it’s MIT man, you know it’s gonna be interesting! I’ve been a member of the MIT Enterprise Forum for about two years now. While not all their events interest me, specifically the bio-tech stuff, they do host many very helpful and relevant events and networking opportunities. From big, globally broadcasted panels on angel investing and venture funding, to small networking opportunities where David Weinberger shares his perspective on the digital world, MIT Enterprise Forum is well worth your attention.
  • MIT Entrepreneurship Center – Cambridge, MA. Are you an entrepreneur? Doesn’t really matter what industry you’re in – go to these events! Get involved! There’s a ton of value to be gained at this event. If you’re in the Boston area – don’t be a schmuck, take advantage of all the MIT has to offer!
  • The Capital Network – Waltham, MA. An organization for entrepreneurs seeking funding. I had the honor of being on one of their recent panels and I thoroughly enjoyed myself. TCN offers some really powerful resources for entrepreneurs, and they really take their time to make sure you’re absorbing all that you can. It’s very much a dialogue at TCN.
  • TechTuesday – An event hosted by the Mass Technology Leadership Council and growing in strength and numbers.

Here’s a bunch more (write-ups courtesy of Don Dodge, thanks Don!):

New England Angel Capital Conference – The Angel Investor groups of greater Boston meet once a quarter to review their best companies. Each group nominates companies to present. They are all looking for a round of funding that is bigger than any one Angel Group can handle. This meeting lets all the groups get a look at promising companies and pool their investment dollars.

Entrepreneurial Team Building – a panel of entrepreneurs that have built companies from the ground up and know the ins and outs of building great teams. What really makes a team come together? How can you be sure that you are bringing in the right folks? Who should be hired first, second, next? We’ll talk about teams at the senior management level and at the BOD level.

Entrepreneurial Series – Plain English Term Sheets – This is a webinar for startup entrepreneurs who want to understand the details of financing term sheets. What to ask for…and what to avoid.

MITX – Mass Innovation & Technology Exchange have lots of great events for technology based startups. The next session is “Building Social Applications and Widgets“.

The 128 Innovation Capital Group – The regular meetings are held on the second Thursday of every month at the Best Western Hotel on Totten Pond Road in Waltham. Every month an investor provides our formal program. After Q&A, our speaker generally remains to speak with audience members, one on one. After the meeting, a roster with the contact information of all attendees is made available to those who came to the meeting.

Nantucket Conference – The 2008 Nantucket Conference audience will consist of approximately 150 of New England’s top entrepreneurs, investors, and tech executives. Rather than sitting through a series of speeches and PowerPoint presentations, the audience will be engaged in a dialogue – and sometimes a heated debate – with Conference presenters.

Get out there! Spring is here, so you’re out of excuses!

My Experience at WebInno

So back on November 29th, we at Citysquares had the pleasure of being a ‘side-dish’ at WebInno. Run by David Biesel, the event is, in my opinion, a hugely needed event for beantown. With all the amazing technology companies here in Boston, and the schools and the massive amount of brainpower here, it’s amazing to me that WebInno is really the only one of its kind here. I don’t know if there were other events like this in years past, but man oh man, this was long overdue!

When were were a side-dish at WebInno in November, I really didn’t know what to expect. We were fortunate to have been given the opportunity by David, on the phone, about 2 weeks before the event. We knew we’d have a side table (along with 3 other local startups) and would not be one of the main presenters. But that was fine, we were just glad to have the opportunity to strut our stuff. We wore our polo shirts, had our tchotchkes all lined up on the table, plenty of computing power and some signage from past events. We were also lucky enough to be located next to the bar, which has its own innate benefits. Not 20 minutes into the event, we barely had the laptops powered up, were we getting hammered by the arriving attendees. We didn’t miss a beat though. As the night progressed, and the main presenters did their thing, I found that out of all the side-dishes, we had the most traffic and it was pretty steady all night. I don’t know why, but I can assume it was because a) we were next to the bar, b) we had our attire on, c) we were on our toes, hopped up on coffee, and ready for anything, and d) we could answer every question that was tossed our way, with little or no hesitation. Hey, we’re very well put together!

The crowd was largely made up of local techies, but not the IT kind, not the biotech kind, the dot-com kind – and more so, the web 2.0 kind. Hipsters young and older, big thinkers, new entrepreneurs, veteran entrepreneurs, and yes, there were a small handful of service providers (buy they behaved themselves). Having “CEO” clearly printed on my name tag brought an overwhelming amount of attention and quizzing from all of the above. I was peppered long and hard with questions ranging from “what is your business model?” or “how many cities are you in?” or “how many advertisers do you have?” or “so how to you get to critical mass?” to “are you funded?” All questions I enjoyed fielding. Chris and Bob were busy doing the same thing – fielding questions and suggestions from everyone. They were cool, calm and collected, and having a ball.

At about 9:30pm, I was engaged in a conversation with Nabeel Hyatt and a friend of his from Yahoo!, and I looked around and noticed the hotel staff had begun cleaning up the room and we were the only company left! I was shocked! Three straight hours of talking, selling to the crowd, and no dinner. I was exhausted but also exhilarated.

After the event Chris, Bob and I went to grab a burger and a beer to wind down and try to reflect on the experience. The word “whirlwind” was used many times.

Of all the intensity and excitement of the evening, we walked away with two valuable and intangible results:

  1. We received an unbelievable amount of positive feedback and energy from virtually every single person who came by. Across the board, everyone was impressed with what we’ve accomplished with what little we’ve had to work with, and we were reminded just how far we’ve come in the 13 months since we launched. It’s hard to explain how thankless sometimes running a startup can feel – how grueling, and stressful it can be for us as professionals, and in our personal lives. The WebInno reminded us what it’s all about, and just how far we’ve come and how important our mission and vision really is. That is so valuable.
  2. Connections connections connections. We met so many people and made so many powerful and valuable connections. I met CEO’s of companies that have been on my radar for many months, investors, service providers, and many entrepreneurs who are confused or struggling to get out of the gates, and entrepreneurs who’ve been-there-and-done-that. Now, two months later, I’ve been able to further many of those relationships along. One of them is blossoming into a new adviser to Citysquares, another is looking like a potential business development partnership, and many others are turning into early friendships based on mutual interests.

Last night I had the pleasure of returning to WebInno, but not as a presenter or side-dish, rather as an attendee. I met up with a few people I had planned to meet there, and with little delay, the whirlwind began again. Prior to the first presentation by GuildCafe, I met up with our PR consultant Matt Ellis. I told him about the event a few weeks ago and he seemed very glad to be in on the secret. After the presentations I was swept back up in the energy of the room and was approached by people I’d met at the last event, and, overwhelmingly, people I hadn’t met at the last event but who’d heard of Citysquares and had questions or comments about the site. Again, the energy was palpable and fun. Last night, the crowd was about 30% more than last time!

The “Main Dish” presenters were as follows:

  1. GuildCafe. Presented by Jon Radoff. A very well designed, seemingly very infectious social networking platform for online game players. What I love about GuildCafe is the immensity of the market! No doubt, online gaming is big, and getting bigger. I strongly believe that in 2007 online gaming, especially MMORPGs, will capitivate a worldwide audience and, much like MySpace did two years ago, really shake things up. GuildCafe is poised to leverage this momentum and build a very large, sticky, social network for gamers. I look forward to seeing them blossom! Jon Radoff did a great job presenting – very charismatic and good humored.
  2. Punchbowl Software. Presented by Matt Douglas. is a new web application that provides an easy, comprehensive, and personal way to plan an at-home party. Matt did a nice job presenting this (pardon the comparison) evite on steroids. That’s the only brief way I can word it. It’s a unique twist on the online invitation model, in that it provides quite literally everything you might need at your finger tips to plan a party. I have to say that the use of AJAX was a bit over the top. I like punchbowl, but I wonder if it’s just a little too much? evite did what they did (and continue to) because it’s simple – its easy and it doesn’t require too much thought or time. I have to plan a graduation party for my wife soon, and hey – I just may use punchbowl! So we’ll see if I can deal! Another great software that I have found is the SalonTouch Studio Software, it has everything I need.
  3. Goombah. Presented by Diane Sammer. Goombah is an exciting new product for music discovery, music, promotion, and social networking based on music taste similarities. Goombah is cool, but the first thing that jumps out at me is the word “goombah” – the offensive use of the word. That aside, right now Goombah is entirely dependant on iTunes. I, for one, am not a fan of iTunes and the iPod – for many reasons. Goombah is onto something here though – I like the idea of being able to look at music that other people are listening to, who share my music tastes. I have 18 GB of music on my server here, and sometimes, believe it or not, I get bored. That’s when I use Rhapsody and tune into some channels. I’d love the ability to find others who like the same music that I do and check out some stuff they have that I don’t. If Goombah works with Rhapsody someday, I’ll give it a shot.

The side-dishes were DoodleBoard, Geezeo, MobaTalk, SpotStory, and TrustPlus. As I mentioned earlier in this post, I got swept up in the whirlwind and just didn’t have a chance to talk to any of the side-dishes with the exception of a brief chat with SpotStory at the end of the evening.

Anyway, that’s my long (very long) review of the WebInno event. I definitely plan to keep attending these events. But don’t think I’m going to be this verbose after each event. Wink